有机光电催化合成研究进展

doi:10.6023/cjoc202310034

摘要/Abstract

有机光电催化合成是一种将电催化与光催化合成策略相结合的新型反应模式, 目前关于此类反应的研究仍处于起步阶段. 近几年, 随着该策略的兴起, 越来越多的报道证明了这种新型反应模式的可行性与其实现新反应的潜力. 利用光能和电能作为反应的驱动力, 无需使用化学计量的氧化剂或还原剂, 该策略能够在相对温和的条件下实现有效且高选择性的氧化还原反应, 被广泛应用于氧化还原及偶联反应等众多反应体系. 总结了近些年有机光电化学合成的最新研究进展, 根据反应的成键类型进行系统分类, 并介绍反应机理及其优势和特点, 最后对该研究方向的发展进行了展望.

关键词: 有机光电催化, 电化学合成, 光化学合成, 协同催化

Organic electrophotocatalysis synthesis is recognized as a powerful and scalable methodology for organic synthesis combining photocatalysis and electrolysis synthesis. However, the research in organic electrophotocatalytic synthesis is still in an early stage. In recent years, with the emergence of this strategy, an increasing number of reports have demonstrated the viability and potential of this new methodology to achieve unprecedented transformations. By harnessing light energy and electric energy as driving forces for the reaction, without relying on stoichiometric oxidants or reductants, it enables effective and highly selective redox reactions under relatively mild conditions. Consequently, it finds wide applications in various reaction systems including redox and cross coupling reactions. A comprehensive overview of the latest advancements in organic electrophotocatalysis synthesis in recent years while categorizing the reactions based on their bonding types is provided. The reaction mechanism, advantages and characteristics are also introduced. Finally, the future development direction of organic electrophotocatalytic synthesis is prospected.

Key words: organic electrophotocatalysis, electrochemical synthesis, photochemical synthesis, synergistic catalysis

引用此文

叶增辉, 刘华清, 张逢质. 有机光电催化合成研究进展[J]. 有机化学, 2024, 44(3): 840-870.

Zenghui Ye, Huaqing Liu, Fengzhi Zhang. Recent Advances in Organic Electrophotocatalytic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 840-870.

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图/表 41

图1. 有机光电催化合成文章发表趋势

Figure 1. Trends of organic electrophotocatalytic synthesis publication by years

图式1. Moutet和Reverdy课题组报道的有机光电催化反应

Scheme 1. Original electrophotocatalytic transformations reported by Moutet and Reverdy

图式2. 光电催化维生素B12介导酰基自由基共轭加成反应

Scheme 2. Electrophotocatalytic vitamin B12-catalyzed conjugate addition of acyl radicals

图式3. 光电催化杂芳烃的Minisci烷基化反应

Scheme 3. Electrophotocatalytic Minisci alkylation of heteroaromatics

图式4. 光电催化芳烃三氟甲基化反应

Scheme 4. Electrophotocatalytic trifluoromethylation of aromatics

图式5. 光电催化醚类Minisci反应

Scheme 5. Electrophotocatalytic Minisci reaction of ether

图式6. 光电催化C(sp3)—H键芳构化反应

Scheme 6. Electrophotocatalytic C(sp3)—H arylation

图式7. 光电催化脱羧Minisci反应.

Scheme 7. Electrophotocatalytic decarboxylative Minisci reaction

图式8. 光电催化苯并噻唑烷基化反应

Scheme 8. Electrophotocatalytic alkylation of benzothiazoles

图式9. 光电催化多氟芳烃脱氟芳基化反应

Scheme 9. Electrophotocatalytic defluorinative arylation of polyfluoroarenes

图式10. 光电催化脱氨基Minisci反应

Scheme 10. Electrophotocatalytic deaminoalkylation Minisci reaction

图式11. 光电催化环状醇开环官能团化

Scheme 11. Electrophotocatalytic ring-opening functionalization of cyclic alcohols

图式12. 光电催化含氮稠环化合物的合成

Scheme 12. Electrophotocatalytic synthesis of nitrogen containing fused compounds

图式13. 光电催化脂肪羧酸脱羧与芳基溴代物偶联反应

Scheme 13. Electrophotocatalytic decarboxylative coupling of aliphatic carboxylic acids with aryl bromides

图式14. 光电催化对映选择性脱羧氰化反应

Scheme 14. Electrophotocatalytic enantioselective decarboxylative cyanidation

图式15. 光电催化烯烃对映选择性氰化芳基化反应

Scheme 15. Electrophotocatalytic enantioselective cyanidation and heteroarylation of olefins

图式16. 光电催化苄位C(sp3)—H键对映选择性氰基化反应

Scheme 16. Electrophotocatalytic enantioselective cyanidation of benzyl C(sp3)—H bond

图式17. 光电化学Ce催化烷烃合成烷基苯并咪唑稠环化合物

Scheme 17. Photoelectrochemical Ce-catalyzed for the synthesis of alkylbenzimidazole fused rings

图式18. 光电催化TAC介导芳烃-唑类C—H/N—H偶联反应

Scheme 18. Electrophotocatalytic TAC-mediated aromatic-azole C—H/N—H coupling reaction

图式19. 光电催化TPA介导烯烃-唑类C—H/N—H键偶联反应

Scheme 19. Electrophotocatalytic TPA-mediated olefin-azole C—H/N—H coupling reaction

图式20. 光电催化未活化芳基氟化物的SNAr反应

Scheme 20. Electrophotocatalytic SNAr reaction of unactivated aryl fluorides

图式21. 光电催化HLF反应

Scheme 21. Electrophotocatalytic HLF reaction

图式22. 光电催化C(sp3)—H键叠氮化反应

Scheme 22. Electrophotocatalytic azidation of C(sp3)—H bonds

图式23. 光电催化芳烃官能团化反应

Scheme 23. Electrophotocatalytic aromatic functionalization reaction

图式24. 光电催化Ritter型C—H胺化反应

Scheme 24. Electrophotocatalytic Ritter-type C—H amination reaction.

图式25. 光电催化邻近C—H二氨基化反应

Scheme 25. Electrophotocatalytic diamination of vicinal C—H bonds

图式26. 光电催化芳基烯烃氨氧化反应

Scheme 26. Electrophotocatalytic aminooxygenation of aryl olefins

图式27. 光电催化脂肪族羧酸脱羧叠氮化反应

Scheme 27. Electrophotocatalytic decarboxylative azidation of aliphatic carboxylic acids

图式28. 光电催化芳烃C—H胺化反应

Scheme 28. Electrophotocatalytic C—H amination of aromatics

图式29. 核黄素/硫脲协同光电催化羟基氧化

Scheme 29. Electrophotocatalytic alcohol oxidation with riboflavin/thioureas

图式30. 光电催化芳香烃乙酰氧羟基化反应

Scheme 30. Electrophotocatalytic acetoxyhydroxylation of aromatics

图式31. 多个相邻C—H键的光电催化氧化

Scheme 31. Electrophotocatalytic oxidation of multiple adjacent C—H bonds

图式32. 光电催化杂芳烃与醛的羟基化反应

Scheme 32. Electrophotocatalytic hydroxylation of heteroaromatics with aldehyde

图式33. 光电催化烯烃环氧化反应

Scheme 33. Electrophotocatalytic epoxidation of olefins

图式34. 光电催化烯烃环氧化反应

Scheme 34. Electrophotocatalytic epoxidation of olefins

图式35. 光电催化芳基卤化物还原官能团化反应

Scheme 35. Electrophotocatalytic reductive functionalization of aryl halide

图式36. 光电化学NpMI催化卤代芳烃还原官能团化.

Scheme 36. Electrophotocatalytic NpMI-catalyzed reductive functionalization of aryl halides

图式37. 光电化学PDI催化卤代芳烃还原官能团化.

Scheme 37. Photoelectrochemical PDI-catalyzed reductive functionalization of aryl halides

图式38. 光电化学4DPAIPN催化芳基季铵盐或芳基膦酸酯的还原官能团化

Scheme 38. Electrophotocatalytic 4DPAIPN-catalyzed reductive functionalization of aryl ammonium salt and aryl phosphonates

图式39. 光电催化磷酸烷基酯的还原反应

Scheme 39. Electrophotocatalytic reduction of alkyl phosphates

图式40. 光电催化C(sp3)—H硼化反应

Scheme 40. Electrophotocatalytic C(sp3)—H boronation

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